2,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propanal → (12Z,15Z)-1,2-bis((9Z,12Z)-octadeca-9,12-dienyloxy)henicosa-12,15-dien-3-ol

HRID 1259007노트

반응식

HRID 1259007 반응식
[CH2:1]([O:19][CH:20]([CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:21]=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>C(OCC)C>[CH2:25]([O:24][CH2:23][CH:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:21]([OH:22])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

참가 물질

3

반응물 1

HCID 866675312,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propanal

생성물 1

HCID 86667532(12Z,15Z)-1,2-bis((9Z,12Z)-octadeca-9,12-dienyloxy)henicosa-12,15-dien-3-ol수율 41.9%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution of 2,3-bis((9Z,12Z)-octadeca-9,12-dienyloxy)propanal (1.5 g, 2.62 mmol) in anhydrous diethyl ether (10 mL) was added LinMgBr Grignard (2.56 mL, 5.23 mmol). Upon completion, the solution was quenched with 5% HCl (50 mL) and washed with diethyl ether (3×50 mL). The combined ethyl ether extracts were dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography on silica gel 60 (eluted with a gradient of 100% hexanes to 2% ethyl acetate in hexanes) to afford (12Z,15Z)-1,2-bis((9Z,12Z)-octadeca-9,12-dienyloxy)henicosa-12,15-dien-3-ol as a colorless oil (460 mg, 21%).

후처리

  1. customUpon completion, the solution was quenched with 5% HCl (50 mL)
  2. washwashed with diethyl ether (3×50 mL)
  3. dry with materialThe combined ethyl ether extracts were dried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to dryness
  6. customThe residue was purified by column chromatography on silica gel 60 (
  7. washeluted with a gradient of 100% hexanes to 2% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-e86d404cd86c4373b20a43cd74db9be4
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466122B2

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